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Diastereoselective synthesis of erythro- and threo-2-hydroxy-3-methyl-4-pentenoic acids by the ester enolate claisen rearrangement of 2-butenyl 2-hydroxyacetate

✍ Scribed by Toshio Sato; Kazuhisa Tajima; Tamotsu Fujisawa

Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
148 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

The ester enolate Claisen rearrangement of IE)-and IZ)-2-butenyl

2-hydroxyacetates gave erythro-and threo-2-hydroxy-3-methyl-4-pentenoic acids with high diastereoselectivity

via silyl ketene acetals, respect<vely.

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Asymmetric Syntheses via Heterocyclic In
Asymmetric Syntheses via Heterocyclic Intermediates, XXXIII. Asymmetric Synthesis of (Diastereomerically and Enantiomerically Virtually Pure) Methyl (2R,3S)-threo-2-Amino-3-hydroxy-4-alkenoates by the Bislactim Ether Method
✍ Schöllkopf, Ulrich ;Bardenhagen, Jürgen 📂 Article 📅 1987 🏛 John Wiley and Sons 🌐 English ⚖ 534 KB

The titanium derivative 4a of the bislactim ether l a from cyclo-(L-Val-Gly) reacts with + m a t u r a t e d aldehydes 5 exclusively by 1.2-addition in a highly diastereowlective mode to give virtually only the (2R,l'S) diastereomers of type 6. Upon hydrolysis these furnish the methyl (2R,3S)-thrm-2